Ed Batista

Stow the Oars, Raise the Sails (On Leaving a CEO Role)

A client is in the process of transitioning out as the CEO of the company he founded. He previously negotiated a sale to a corporate parent, which achieved his financial goals for the business while allowing it to continue operating independently and positioning him as a shareholder of the parent.

He's delegated managerial duties to his hand-picked successor, he's preparing to step into an executive chair role, and he's confident that this is the right move at the right time. He feels optimistic about the future of the business...and yet he's also had the nagging feeling that something was off, and a recent coaching session helped to illuminate the issue.

I suggested that Joseph Campbell's concept of the Hero's Journey might be useful in exploring his situation. Campbell was an American scholar who applied the insights of psychology to his study of mythology, folklore and religious traditions from around the world, and I find his ideas highly relevant to my work with leaders. [1]

In the Hero's Journey, also known as the monomyth because it appears so frequently in so many different cultures, we meet the hero in their ordinary existence, the "World of Common Day," as Campbell called it. The hero is "called to adventure," and if they heed the call they venture forth into a "Region of Supernatural Wonder," where they encounter various allies and adversaries in the course of a series of struggles in search of a "boon," a trophy or prize to be shared:

When the hero-quest has been accomplished...the adventurer still must return with their life-transmuting trophy. The full round, the norm of the monomyth, requires that the hero shall now begin the labor of bringing [their prize] back into the kingdom of humanity, where the boon may redound to the renewing of the community. [2]

This led to a discussion with my client of leadership as a journey, with a destination, a goal, and a conveyance, a means of making progress along the path. As a founder and CEO, my client was an oarsman, straining hard to propel his craft forward. It was arduous work, but it had certain advantages. The destination was far in the distance over the horizon, but the compass pointed straight to it: the survival and ultimate success of the company. The goal was by no means certain to be achieved, but it was commonly understood: financial returns sufficient to meet the needs of all stakeholders.

There was another advantage to the work of an oarsman: my client's labors were clearly visible to all. Anyone with an interest in my client or the company could see that he was constantly striving and doing his best. There was never any question about his work ethic, his commitment, or his values. And yet having completed his "hero-quest" through the sale of the company, my client now found himself in uncertain territory. Retiring to a life of leisure held little appeal for him. While this may seem surprising to some, it's a common response among my clients:

We have a number of preconceived notions about what it would be like to not have to work, and they're often some form of "life as permanent vacation." That's certainly what some people do when they realize a windfall, and if it brings them joy, then good for them. But that's not what I've observed in my practice. It turns out that many people who've worked hard their entire careers have a finite capacity for being on vacation. [3]

When people like my client have achieved a degree of financial freedom, they still need to make a contribution through some form of work. But simply continuing on as an oarsman would pose inevitable difficulties. My client's successor was ready and able to take up the oars himself. He was eager to benefit from my client's guidance as executive chair, but he also wanted a degree of autonomy and independence as CEO. My client would have to determine how to add value in this new capacity without holding on to an oar. [4]

My client also has a role to play as a shareholder in the parent, but he realized that approaching it as an oarsman would be the wrong mindset. It would occupy more time and energy than necessary and distract him from the essential project of finding a new sense of purpose, a new identity. While he won't be "retired," he may elect to remain in the "World of Common Day," sharing what he learned on his quest and stepping into the role of teacher or sage. [5] Or he may find himself called to pursue another venture in the "Region of Supernatural Wonder" and embark on a new quest.

With these and other options now available to my client, he's realized that he must change how he thinks about work, which entails a change in how he thinks about himself. He's still on a journey, but not as an oarsman. It's time to stow the oars and raise the sails. The sailor doesn't just go where the breeze takes him, of course. He is an active navigator, but he must be open to possibilities, sensing and responding to the prevailing winds. Under the right conditions he can change course rapidly. And he can travel vast distances, enabling him to pursue a wider range of destinations.

And yet while this new way of thinking offers certain benefits, it also poses challenges. The sailor can make more progress than an oarsman, but the path he takes is far less predictable. The ability to change course and travel farther requires a greater tolerance for ambiguity and uncertainty. And while the sailor plays an active role with his hand on the tiller, his efforts aren't always visible. To the untrained eye it may look like he's just sitting there, which can be unnerving to the veteran oarsman.

But even these challenges play an important part in the process of bringing one Hero's Journey to a close and preparing for the possibility of another. Campbell notes that the hero's successful return is by no means an easy transition: "The first problem of the returning hero is to accept as real, after an experience of the soul-satisfying vision of fulfillment, the passing joys and sorrows, banalities and noisy obscenities of life." [6]

The oarsman struggles mightily against the current, but he enjoys the struggle, in part because it keeps the "banalities and noisy obscenities of life" at a distance. It can be tempting to keep them at bay by holding tightly to the oars, imagining that this remains duty of a hero. The new challenges posed by sailing remind the hero that they must adapt to their new circumstances.

 

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Footnotes

[1] The Hero's Journey in Everyday Life

[2] The Hero with a Thousand Faces, page 167 (Joseph Campbell, New World Library, Third Edition, 2008)

[3] What Do You Need When You Don't Need the Money?

[4] The Ambiguous Role of Executive Chair

[5] The Warrior and the Sage

[6] Campbell, page 189.

 

Photo by Alvin Trusty.

You Don't Have to Do All the Thinking Yourself

Most of my clients are CEOs, and many of them are founders, and they're almost invariably high-agency people who enjoy taking on responsibility and prefer to be in charge. This is consistent with research by psychologist Jerry Burger which showed that differences in the need for control have a significant impact on behavior and attitudes, and that people who score high on this scale are more likely to become leaders:

People with high desire for control were found to have a higher aspiration level, to respond to challenges with increased effort, to persist longer at difficult tasks, and to make attributions for task outcomes that facilitate future striving for achievement. [1]

This is also consistent with David McClelland's "motivational needs theory," which suggests that people are driven primarily by three distinct needs [2]:

• The need for power, or concern "about having 'impact, control, or influence over another person, group, or the world at large.'" [3]
• The need for affiliation, "or the need to be with people" and a concern with "establishing, maintaining, or restoring a positive affective relationship with another person or persons." [4]
• The need for achievement, or "doing something better for its own sake, or to show [that one] is more capable of doing something." [5]

McClelland also studied people's capacity for "activity inhibition," or impulse control, and his research showed that the most successful senior leaders display 1) a relatively high need for power, 2) a relatively low need for affiliation, and 3) a high degree of impulse control, a distinctive pattern that he called "leadership motive syndrome." McClelland found that people who possessed this combination of traits were most likely to obtain senior leadership positions, ultimately outpacing those who merely had a high need for achievement. [6]

But another theme in my work is that our weaknesses are often overused strengths, a concept I first learned from my mentor and colleague Carole Robin. And while a high degree of agency and a desire to exert control can be "leadership superpowers," like all such traits they have "shadow sides." [7] One such shortcoming is a leader's perception that it's their responsibility to come up with the best ideas and solve problems on their own.

Leaders obviously have a special role to play in any problem-solving process, particularly early-stage founders whose visions for the venture may still reside largely in their heads and whose teams may lack sufficient context or expertise to act independently. But when this state of affairs persists, the leader may become a bottleneck, an unqualified decision-maker, or an outdated expert. [8] So if you're sensing that this might be a challenge for you, what can you do?

1. Look in the Mirror (and Ask for Feedback)

A starting point is assessing the extent to which your sense of agency and preference for control might be inhibiting more effective means of problem-solving. This entails being more self-aware of your impact on the people around you. [9] And note that your self-perception almost certainly includes some blind spots, so be sure to ask those people for input. In my first leadership role after business school I was lucky to have a mentor on my Board of Directors who took me aside and gave me this precise feedback. (He also advised me to address it by working with a coach, which was my first exposure to coaching.)

2. Invite Others Into the Problem (Even When They're "the Problem")

I'm not suggesting that you simply delegate problem-solving to others. They may not be ready, and you may be unhappy with the results. But in between A) deciding in isolation and telling people what to do, and B) delegating and hoping for the best, there are a range of alternatives: sell, consult, agree, advise, and inquire, to be specific. [10] I ask clients to consider how they might use one of these methods to "invite others into the problem" as a way to test their readiness and capacity.

This is possible even when other people themselves are "the problem." Another theme in my practice is the ubiquity of interpersonal conflicts between leaders and key stakeholders, from employees to investors. In you're in such a situation it's not possible to delegate the issue, but it's also not necessary for you to do all the work on your own. You can invite others to join you by being overt about your goal of improving the working relationship [11], by giving (and requesting) more candid feedback [12], and by discussing potential differences in your work styles that are likely contributing to the conflict. [13]

3. Foster a Better Problem-Solving Culture

Leadership teams vary widely with regard to their ability to problem-solve as a group, and this is one manifestation of their culture, as defined by management expert Michael Watkins:

Culture is consistent, observable patterns of behavior in organizations... Culture is [also] a social control system. Here the focus is the role of culture in promoting and reinforcing "right" thinking and behaving, and sanctioning "wrong" thinking and behaving. Key in this definition of culture is the idea of behavioral "norms" that must be upheld, and associated social sanctions that are imposed on those who don’t "stay within the lines." [14]

As the leader you don't dictate the culture, but you have a great deal of influence over it, particularly if you're a founder. So consider the following:

• Do you have the right people in the room or on the call? Optimally your leadership team includes the most relevant and useful voices, but sometimes junior people have vital information and need to be included, and sometimes nominally senior people are just in the way and shouldn't be there.
• Do you have the right people on the team? If there's a persistent mismatch between the composition of your leadership team and the most relevant and useful voices, that may be a sign that it's time for a change. [15]
• Is everyone contributing constructively? Is anyone dominating (including you)? Is anyone being repeatedly interrupted or ignored? As the leader you have to be attuned to these group dynamics, because you're the person who's best-positioned to intervene and facilitate as needed. [16]
• Do people feel free to disagree (especially with you) and to share bad news? This is what we actually mean by "psychological safety." [17]

4. Prioritize and Upgrade Your Own Reflection Time

Involving others in problem-solving doesn't mean you'll no longer engage in solo reflection. If anything, you should be able to devote your individual problem-solving time to even more meaningful and significant issues than before. But it's common for highly responsible leaders to deprioritize this time, to push it to the far corners of their calendar, or to allow it to come at the expense of personal obligations.

Here the key is recognizing that your attention is one of your organization's most precious resources, and it's up to you to be its steward. Very few others will care (or even notice) that your attention is finite, and that any time taken from solo reflection and directed toward other activities comes at a high cost. You have to be deliberate about protecting open space for this purpose [18], and creating the conditions that allow you to do your best thinking. [19]

 

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Footnotes

[1] The Effects of Desire for Control on Attributions and Task Performance (Jerry Burger, Basic and Applied Social Psychology, 1987)

• This quote from Burger's 1987 paper describes research conducted previously and discussed in detail here: Desire for Control and Achievement-Related Behaviors (Jerry Burger, Journal of Personality and Social Psychology, 1985)

[2] For an extensive discussion of each of these needs, see Human Motivation, Chapters 7-9 (David McClelland, 1987). Having developed his "motivational needs theory" around these three drives in the 1960s and '70s, later in his career McClelland suggested that a fourth such drive is the "avoidance motive," characterized by a fear of failure and a need to minimize anxiety and reduce distress (and discussed in Human Motivation, Chapter 10.) However, while McClelland's research on leadership identifies a relationship among the first three needs, he doesn't integrate the avoidance motive in the same way, nor is it included in most discussions of his theory, so I've omitted it here as well.

[3] Ibid, page 271. (McClelland cites a definition made by his colleague and former student David Winter: The Power Motive, 1973.)

[4] Ibid, page 347. (McClelland cites a definition made by his longtime collaborator John Atkinson with Roger Heyns and Joseph Veroff: The effect of experimental arousal of the affiliation motive on thematic apperception, The Journal of Abnormal and Social Psychology, 1954.)

[5] Ibid, page 229.

[6] Ibid, page 313:

"By way of contrast, those with high n Achievement peaked in their careers [earlier]. The nonlinear trend is significant. The explanation seems to lie in the fact that individuals high in n Achievement are used to doing things by themselves and for themselves... They are able to advance in the company as long as their job involves the individual contributions they make. However, at higher levels the focus on the job shifts to influencing others. The greater success of those with the leadership motive syndrome at this level can be explained on the grounds that they are interested in influencing others (the high n Power score), they are not unduly concerned about whether they are liked or not (the low n Affiliation score), and they are self controlled (the high Activity Inhibition score)."

[7] Superpowers and Shadow Sides

[8] How to Scale: Do Less, Lead More

[9] The Balcony and the Dance Floor

[10] Leadership, Decision-Making and Emotion Management

[11] Better Working Relationships

[12] How to Deliver Critical Feedback

[13] Work Style Differences

[14] What Is Organizational Culture? (Michael Watkins, Harvard Business Review, 2013)

[15] The Evolution of the Executive Team

[16] For more on group dynamics:

• Group Dynamics: The Leader's Toolkit
• Group Dynamics: Very Loud (and Very Quiet) People

[17] Safety Is a Resource, Not a Destination

[18] Open Space, Deep Work, and Self-Care

[19] How to Think (More on Open Space and Deep Work)

 

Photo by Mike Dish.

On Leadership Transitions and Public Narratives

I work with clients in open-ended engagements that typically last for several years. Either the client or I can elect to conclude our work together at any time, but I've found that my approach is a good fit for leaders who want a long-term thought partner. As a result, although most clients enter my practice occupying a leadership role that they expect to hold for the foreseeable future, I regularly accompany clients as they transition out of that role into a new chapter of their lives.

In some cases a client's transition occurs in parallel with or is triggered by a business event, such as the sale of the company. Many of these situations provide a sufficient explanation for my client's decision to leave their role. The CEO of an acquired company will likely stay on for a period of time to ensure a smooth handover, and if they leave shortly after the transaction no one wonders why. The change in the business is sufficient explanation.

But in other situations a leader's departure will invite curiosity, and this is particularly true if the transition occurs in the absence of a corresponding business event. When this happens, anyone with a reason to care will begin to ask a series of questions. If these questions aren't raised publicly, they will certainly be raised in private:

• Why is the leader leaving? What does it mean?
• Did the leader initiate the transition, or was it initiated by other stakeholders?
• If the leader initiated the transition, do they lack faith in the business? Are they disgruntled or unhappy in some way?
• If others initiated the transition, do they lack faith in the leader? Did the leader fall short of expectations in some way?
• What are the implications for the future? How will the leader's departure affect the business? How will this transition affect the leader's career?

These questions are often problematic. The situation may be sufficiently complex that the answers are unclear, or different parties may have different answers. The answers may be embarrassing to one party or another, or the fact that there are different answers may itself be embarrassing. This can result in paralysis, with the questions hanging in the air, unresolved.

If these questions go unanswered by the leader or the company, other parties will be left to draw their own conclusions. As my colleague Carole Robin says, in the absence of data we make shit up. So in these situations what's required is a public narrative that provides an explanation for the transition that is sufficient to answer these questions (and any number of others that may arise). Note that this narrative isn't fictional or phony, but it is reductive. It leaves out information that may be confusing or distracting in order to emphasize specific aspects of the situation that provide a coherent explanation. In this sense a narrative is a story, and as I've written before,

Why is storytelling such a powerful process? Because we depend upon narratives to navigate the world--they are our compass in the wilderness, our lantern in the dark. Organizational psychologist Karl Weick called this "sensemaking": we rely upon narratives to "make sense" of ambiguous situations and pursue a plan of action in coordination with others. But our reliance on narratives means that in the absence of a coherent story we will feel lost and ungrounded. [1]

So if you're a leader about to embark upon a transition--or if one has been imposed upon you--what should you do? First, envision the various parties who may have an interest in your transition arrayed around you in a series of concentric circles. People in the innermost circle are there because you trust their discretion and their judgment, and their interests are fully aligned with yours. This space will accommodate a great deal of complexity and nuance, and you benefit by being as candid as possible with the people who occupy it, in part because they will be able to advise you on how to communicate with others.

As you go further out, in each subsequent circle there's a little less trust and a more divergent set of interests. There's less capacity to handle complexity and nuance. As a result, you'll need adjust what you share with the people in that circle by modifying the narrative. Typically this entails reduction--leaving out certain aspects of the situation in order to emphasize others. This ultimately results in a series of narratives that explain your transition to different sets of stakeholders in terms that fit their ability and willingness to comprehend the situation and are appropriate to your relationship with them.

These narratives will get more reductive the further out you go, but it's important that they're all mutually consistent. They shouldn't contradict each other, nor should they contain falsehoods. I don't make this assertion out of naive idealism, but out of pragmatism. Contradictory narratives or those that are demonstrably false risk the loss of trust and create unnecessary complications that can usually be avoided with a modest amount of forethought.

The outermost circle is the public sphere, occupied by individuals you don't know personally, but who for some reason have an interest in your transition. The narrative for the public sphere is generally reductive to the point of simplicity. Thus the cliché, "I want to spend more time with my family." That's almost always true, and it's rarely the whole truth.

I'll add that I often see leaders make three mistakes in this process:

They wait too long.

Leadership roles are hard to obtain, but they can be even harder to leave. Leaders tend to feel a high degree of responsibility for the business and their stakeholders, and they don't want anyone to feel let down, misled, or betrayed by their departure. They want the narrative to reflect "good timing," so they wait for (or try to engineer) a moment when no one will fault them for leaving. But that moment may never come, and the leader may find that the situation gets worse, not better. A theme in my practice is that sometimes there are no good options, only varying degrees of bad. The goal isn't "success," but "avoiding catastrophe." I don't advise acting with undue haste, but I do encourage clients to consider the potential costs of delay. [2]

They pretend they're invulnerable.

I'm under no illusions about the risks to a leader of being perceived as weak or incapable. [3] But leaders in transition can also err by insisting on a narrative that rejects any hint of vulnerability and represents their career as a seamless trajectory with every move "up and to the right." This can contribute to waiting too long as the situation worsens, but it can have other negative consequences. When a leader's desire for a transition is being driven by a sense of fatigue or burnout, the pretense of invulnerability shuts out stakeholders who may be in a position to offer support and exacerbates the leader's sense of isolation.

They rely on unreliable intermediaries.

I began my career as a journalist, and I've had many friends in the media, so I empathize with the challenges faced by people tasked with explaining events in the business world to their readers and viewers. But it's unrealistic for a leader to rely upon journalists and other intermediaries operating in the public sphere to transmit the leader's narrative--they will have narratives of their own. It's also no longer necessary, as communications and PR expert Lulu Cheng Meservey makes clear:

Today, most of the planet is directly reachable by social media or email. There’s no longer a need to go through traditional gatekeepers of information and brokers of reputation--especially as their own credibility has plummeted... Going direct means crafting and telling your own story, without being dependent on intermediaries. [4]

 

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For Further Reading

Handing Off to a New CEO

The Ambiguous Role of Executive Chair

The Problem with Hot-Swapping (On Exec Transitions)

Footnotes

[1] The Importance of Shared Narrative

[2] Kicking the Can Down the Road (On Hard Decisions)

[3] Cautionary Tales (Authenticity at Work)

[4] Go Direct: The Manifesto (Lulu Cheng Meservey, Flack, 2024)

9,000 Coaching Sessions (The Evolution of a Practice)

Last Thursday, March 13th, I conducted the 9,000th coaching session of my career, and the milestone has prompted a look back at how my practice has evolved over the past two decades. I'm not suggesting that there's one right way to run a practice, or that anything I do should be emulated. But I've always tried to be thoughtful about what will work best for me and my clients, and perhaps these reflections will prove useful to colleagues as they experiment with their approach, or to clients who are curious about what this work looks like from a coach's point of view.

When I conducted my 8,000th coaching session in May 2024, 1:1 coaching was my only professional activity and had been since I last taught MBAs at Stanford in 2021. This was a stark contrast to my orientation when I launched my practice in 2006 under the mantle of "Executive Coaching and Change Management." At the time I envisioned that my work would be split equally between coaching individuals and various types of group engagements.

But as the years passed several factors led me to reset those expectations. My participation in Stanford's Group Facilitation Training Program that same year opened up more opportunities to work with groups at the university, including an invitation to join the first team of Leadership Coaches at the Graduate School of Business, where I'd earned my MBA in 2000. In parallel, it became more difficult to fit group engagements into the space available in my private practice.

These developments weren't accidental, but resulted from deliberate choices made in response to my evolving capabilities and skills, the fulfillment I derived from different types of work, and my growing understanding of the respective markets for these services. I was increasingly drawn toward 1:1 coaching, not only because I felt most capable and fulfilled in that work, but also because it was much more straightforward operationally. Today I regularly talk with aspiring coaches, and I encourage them to be very intentional about their business model.

Over time I concluded that I would be best served by focusing on 1:1 coaching rather than group engagements. Coaching experience compounds rapidly, given the consistency with which issues emerge in leaders' lives. The specific circumstances vary considerably, and all my clients must feel acknowledged as individuals, but I also add value simply by reassuring leaders that many of the challenges they face are quite common.

I accelerated my learning process by writing frequently, ultimately sharing more than 900 essays on coaching and related topics on this site since launching my practice. That's the equivalent of one post per week for nearly 19 years, although I usually write in productive bursts (and my pace has slowed recently, in part because I'm so busy coaching.)

My writing primarily serves two purposes: to integrate and solidify lessons distilled from multiple clients and my reading in a wide range of fields, and to create a library of content to share with current clients that augment our discussions in coaching sessions. I've never written with the expectation that anyone encountering my work would become a client, and that's proven accurate--my referrals have almost all come through word-of-mouth. Nor did I seek to monetize my writing--everything on my site has always been freely available to others under a Creative Commons license.

But this meant that I had to monetize my time, which was another reason why I focused on 1:1 coaching instead of group work in my practice. Coaching is time-efficient, particularly given my use of a flat hourly rate rather than a retainer, and less effort is required for discovery and scoping than in group work. I decided to dedicate some of that time saved to handling all of my practice's logistics, from scheduling to billing. Years ago I considered hiring an assistant as my practice grew but concluded that I preferred owning every aspect of my clients' experience. And so after a decade my practice consisted solely of 1:1 coaching engagements, and I was working with groups almost exclusively at Stanford, with occasional workshops for company founders or leadership teams.

During those initial ten years some of the most rewarding group work I did was facilitating T-groups in Interpersonal Dynamics (aka "Touchy Feely"), and I ultimately spent more than 1,500 hours in that role. One of the reasons I pursued that work so intensively was because I found it highly synergistic with 1:1 coaching. Engaging someone on a challenging topic in a T-group with 12 other people observing and joining in the interaction made the challenges in 1:1 coaching seem easier, and the coaching orientation I brought to T-groups made me a better facilitator.

My practice continued to grow during these years in part because I was honing my skills, but also because I simply said yes as often as possible. This was easier because I'm not a parent, nor did I have many obligations beyond work. My role at Stanford was sufficiently flexible that I could see clients in San Francisco in the morning or evening before or after class. I also began working virtually, holding my initial long-distance coaching sessions via phone or Skype. I assumed that this would always be a minimal part of my practice, but I found that virtual coaching was as effective as in-person, although it was a different experience.

Looking back on this period I joke that as a coach I was a "five-year overnight success," meaning that it took that amount of time to develop the critical mass of former clients who turned out to be the most fruitful source of future referrals. This became evident in 2012 when I began earning more from my private clients than from my full-time role at Stanford, seven years after I started coaching and six years after formally launching my practice.

Despite this development, I opted to stay at Stanford for a number of reasons, including my commitment to the Leadership Labs course and the Leadership Fellows program, which my colleagues and I had helped to establish in 2007. While those initiatives had proven successful, after four years the school wanted us to revamp them, and we spent 2011-12 rolling out a radically different LeadLabs course and integrating Fellows with the pre-existing Leadership Coaching & Mentoring curriculum. These efforts were daunting, but they were also highly energizing and a tremendous source of learning.

The following years also presented me with with some unique opportunities at Stanford. In 2015 I was given a chance to teach my own course, which I called The Art of Self-Coaching. In 2016 I was invited to join the Interpersonal Dynamics faculty and teach the course that I'd facilitated for a decade. And at this point I realized that the balance I'd established in my professional life was no longer tenable--I needed more time for 1:1 coaching in my practice, and that could only come by spending less time with groups at Stanford. So in 2016 I resigned from the full-time role at Stanford that kept me involved with Fellows and LeadLabs, and in 2017 I facilitated a T-group for the last time.

I enjoyed all of that work immensely, particularly the opportunity to guide Leadership Fellows as both a group facilitator and a 1:1 coach. And while each T-group is a unique entity composed of a set of unique individuals, there are a number of patterns that reliably emerge in every group. I'll always be fascinated by group dynamics, and my grounding in this topic makes me far more useful to my coaching clients, who are often seeking to help their leadership teams operate more effectively. But I felt that I had more to learn in other settings, and it was time to move on.

I settled into a new professional routine where I taught one day a week and spent the rest of my time with clients in my private practice. The Art of Self-Coaching proved sufficiently popular that I was invited to teach it in all three academic Quarters, and so in 2017 I stopped teaching Interpersonal Dynamics in order to focus on my course, but the overall balance of teaching and coaching remained the same. These years, 2016 through early 2020, were some of the most gratifying of my career, and I will always view it as a special era. The balance between coaching and teaching was very fulfilling, and although teaching consumed 20 percent of my time and provided 3 percent of my income, it still felt like a fair exchange.

What I enjoyed so much about teaching The Art of Self-Coaching was the opportunity to create the optimal environment for experiential learning, which entailed constant evolution and refinement. I'm not a brilliant lecturer, nor am I particularly gifted at the Socratic method. I am, however, a world-class experiential educator, a role whose closest analogue is perhaps circus ringmaster. The ringmaster merely entertains, of course, and while I was a lively presence in the classroom, my intent was to help my students feel at ease while inviting them to challenge themselves, to go deeper, and to learn more in the process.

I loved being in the classroom one day a week, and I loved the fact that I was able to spend the rest of my time with clients in my private practice. I gave some thought to teaching less often, just once or twice a year instead of three times, because Amy had correctly observed that I ended each Quarter feeling depleted, and my commitment to teaching required me to maintain a waitlist for my practice. So life wasn't perfect, but I was content, and I expected to spend the rest of my career in some form of that arrangement. And then the pandemic hit, and many things changed.

Because I was already conducting roughly one-third of my coaching sessions long-distance, it was relatively easy to go 100 percent virtual. I taught The Art of Self-Coaching virtually in Spring 2020, including a version that I made freely available to the public, and it was a great experience, largely because everyone was coming together to face this unprecedented threat. But I decided to drop down from teaching all three Quarters to just one, primarily because I was exhausted and overwhelmed. My clients were facing the greatest challenges of their careers, and I didn't think I could sustain my support for them while also teaching all year.

I taught virtually again in Spring 2021, and it was not a great experience, largely because I failed to adapt to the needs of students who were also exhausted and overwhelmed. So I took a year off from teaching entirely in order to assess the role I wanted it to play in my life, and in January 2023 I concluded that it was time to retire from Stanford and focus solely on my practice and 1:1 coaching. Sixteen months later I conducted my 8,000th coaching session, and at the time that orientation still seemed right. And then things changed yet again.

In addition to triggering an even sharper focus on 1:1 coaching in my practice, the pandemic led to monumental changes in my personal life. Amy and I left San Francisco, our home for 30 years, and moved to a working sheep and cattle ranch in the far northwest corner of Marin County. It was a deeply affecting experience that taught me much about the natural world, the cycle of life and death, and my evolving identity in middle age. The seclusion we enjoyed was at first simply a respite from the chaos of life under lockdown. But it also allowed me to hone my craft like never before.

I coached all day, every day. I coached more people than ever, from all over the world. I coached more sessions in a day, and more days in a year, than ever before. In 2019, teaching all year and coaching 4 days a week, I held 672 sessions with private clients. In 2020, teaching just once, I held 851 coaching sessions. In 2021, without teaching at all, I held 988 sessions. In 2022 I expanded my hours in order to work with clients in a wider range of time zones and held 1,042 sessions. In 2023 that process continued, and I held 1,132 sessions. Last year I held 1,164 sessions, and I expect to equal that figure in 2025.

In addition to opting out of teaching, working virtually, and expanding my hours, what made this increased workload feasible is that on the ranch I had very few distractions, living among a flock of sheep and a herd of cattle on 250 acres. I think coaches are well-served by living a boring life, and I practice what I preach. And for more than three-and-a-half years it was a wonderful existence, occasionally even magical.

To be sure, rural life posed many challenges, from unreliable Internet to lost sheep to downed tree limbs that trapped us on the property until I learned how to use a chainsaw. We weren't responsible for the livestock, but we were the only full-time residents, so we still had plenty of responsibilities. But Amy grew up on a farm, and I followed her lead, and with the occasional mishap we managed just fine. And yet as we approached the fourth anniversary of our time on the farm, it became clear to me that yet another season of change was upon us.

Focusing my practice on 1:1 coaching while also living on a remote ranch for four years ultimately came to feel somewhat narrow. I still loved coaching, I woke up every day eager to talk with my clients, and I knew I was doing the best work of my career. But eventually I realized that missed the stimulation of group experiences in my personal and professional life, from walking down a busy street to leading a workshop or teaching a class.

This was one of the reasons we decided to leave the ranch in mid-2024 and move to Petaluma, the town of 60,000 people in Sonoma County that had been our primary commercial center while living in the country. And it was also why I considered expanding my practice beyond 1:1 coaching for the first time in many years and began seeking out opportunities to work with groups again.

I explored a range of options, including returning to Stanford. I reached out to a faculty member I knew for guidance, and he was decidedly ambivalent. There were reasons I might want to come back, and there were reasons I might not want to come back, and I might not be welcomed back. Amy was definitely not ambivalent--she thought it was a terrible idea.

I had to conclude that I'd been right in January 2023: "Today I'm struck by the extent to which the courses and programs that were products of the 'new curriculum' are now viewed as features of the landscape, as if they'd always been there. This is gratifying, but it also reminds me that it's time to move on before I, too, am viewed as a feature of the landscape."

I reflected on what I was trying to accomplish in working with groups again. I wanted to work with people like my coaching clients--senior leaders who feel responsible for building a culture that enables their employees to do their best work. I wanted to foster connections between individuals and to create a sense of connection among members of a group. I wanted to draw upon the Art of Self-Coaching curriculum that I'd been developing since 2009. And whatever I did had to be complementary with my existing practice.

The first initiative that came to fruition was a 6-week virtual version of my course, The Art of Self-Coaching for CEOs, which I now offer to small groups of 6 leaders. The first cohort in late 2024 was sufficiently successful that I've planned several more for this year, and Cohort #3 begins tomorrow. I'm still pursuing other efforts, including a retreat for leaders in midlife and collaborating with colleagues to coach a company's leadership team, and I'm contemplating even more, such as a program to help coaches improve how they structure engagements and manage their practices.

We're now nine months into our new lives in Petaluma, and although we miss aspects of life on the ranch--the huge sky, the endless pastures, the addle-headed flock--it's good to have neighbors again and to be able to walk downtown. I know that 1:1 coaching is my ikigai: I love it, I'm good at it, the world needs it, and, happily, I'm paid to do it. And I feel re-grounded with new forms of group work in my professional mix, although I'm increasingly mindful of the limits on my capacity and the need to preserve open space in my life.

But even as I strive to manage my boundaries, as all happy workaholics must, I find it fulfilling to be so busy and am grateful to be of service to my clients. Barring any unexpected developments, I'll conduct the 10,000th coaching session of my career in early 2026. Maybe by then I'll know what I'm doing.

 

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Acknowledgments

Always: Thank you to the hundreds of clients who have entrusted me with the opportunity to play a unique role in your lives and careers. It is truly a privilege that I never take for granted. Thank you to the MBA students with whom I conducted 1,064 coaching sessions at Stanford from 2007 through 2020. I'm thankful to the GSB for bringing us together. And thank you, Amy, for your care and counsel on every step of this journey.

In the Beginning: As a student and early in my career I was blessed with some of the most gifted and caring teachers and mentors a young person could want:

Lloyd Schaefer, Millicent Rinehart, Naomi Duprat, Selby Doughty (Cumberland Valley High School), Tim Dayton (Duke), Richard Lerman (School of the Museum of Fine Arts/Boston), Chris Mauriello, Dagmar Herzog, Tom Simons, Mary Gluck (Brown), the late Don Flaxman, James Van Horne, Joel Peterson, Mary Ann Huckabay, Roberto Fernandez (Stanford), Jerry Fuchs, Kathy Taylor Gaubatz, Vince Stehle, Lynn Labieniec

Getting Started: A number of people played essential roles as I began exploring coaching as a potential path in 2005 and launched my practice in 2006, and I've done my best to pay it forward:

Andrea Corney, Barbara Brewer, Carole Robin, David Bradford, Dietmar Brinkmann, Erica Kisch, Evelyn Williams, Joe Murphy, Justin Sherman, Karin Scholz Grace, Kevin Martin, Lynn Labieniec, Mary Ann Huckabay, Rebecca Zucker, Ricki Frankel, Seth Goldstein, Scott Bristol, Tim Dorman, Vince Stehle

At Stanford: A host of colleagues contributed to my growth and made my work possible at the Graduate School of Business from 2007 to 2021:

Allison Rouse, Amy Kraus, Anamaria Nino-Murcia, Andrea Corney, Agnes Le, Anthony Ramsey, Barbara Brewer, Barbara Firpo, Bob Joss, Bob Sutton, Bonnie Wentworth, Bri' Godfrey, Brian Lowery, Bryan McCann, Carrie Lee, Carole Robin, Chevalisa Bruzzone, Chris McCanna, Chris Sadlak, Christopher Williams, Collins Dobbs, Courtney Payne, David Bradford, Delilah Gallardo, Dietmar Brinkmann, Dikla Carmel-Hurwitz, Domenico Anatrone, Don Hejna, Erica Peng, Evelyn Williams, Garth Saloner, Gary Dexter, Grace Yokoi, Graham Veth, Graham Weaver, Hugh Keelan, Inbal Demri Shaham, Ingrid McGovert, James VanHorne, Jamila Rufaro, Jana Basili, Jed Emerson, Jeff Pfeffer, Jimena Galfaso, Joe Murphy, Joel Peterson, John Cronkite, John Johnson, Johnnie Walton, Joy Hsu, Karin Scholz Grace, Ken Chan, Kevin Martin, Kirstin Moss, Kris Becker, Lara Tiedens, Lela Djakovic, Leslie Chin, Lily Kimbal, Ling Lam, Lisa Kay Solomon, Lisa Radloff, Lisa Schwallie, Lisa Simpson, Lisa Stefanac, Liselotte Zvacek, Lynn Santopietro, Margee Hayes, Marie Mookini, Mark Voorsanger, Mary Ann Huckaby, Melinda Tuan, Michael Terrell, Mike Hochleutner, Mindy Williams, Nancy Dam, Nirit Hazan, Nonna Kocharyan, Nora Richardson, Paul Abad, Paul Mattish, Paul Roberts, Rebecca Taylor, Rebecca Zucker, Rich Kass, Richard Francisco, Richard Haukom, Ricki Frankel, Roberto Fernandez, Sara Stone, Saraswathi Ram Mohan, Scott Bristol, Sharon Richmond, Stephanie Stevens, Sunny Sabbini, Sue Neville, Suzan Jensen, Tony Levitan, Tuquynh Tran, Ursula Kaiser, Vince Stehle, Yifat Sharabi-Levine, Zoe Dunning

My Community Today: I'm privileged to call these people colleagues and friends, and I'm deeply grateful for their encouragement and support:

Agnes Le, Anamaria Nino-Murcia, Andy Sparks, Andrea Corney, Anita Grantham, Annie Riley, Bonnie Wentworth, Brad Stulberg, Brooks Barron, Carole Robin, Cameron Yarbrough, Celine Teoh, Chip Conley, Chris Douglas, Collins Dobbs, Dan Oestreich, Dana Bilsky Asher, Doug Sundheim, Eduardo Andere, Glenn Terrell, Gwen Mellor Romans, Harry Max, Heather Corcoran, Jennifer Ouyang Altman, Jennifer Porter, Joe Dunn, John Baldoni, José Hernandez, Julia Markish, Justin Doyle, Kevin Martin, Khalid Halim, Lauren Weinstein, Lela Djakovic, Lisa Stefanac, Madelyn Sierra, Mario Fraioli, Mary Ann Huckabay, Meredith Whipple Callahan, Michael Chang Wenderoth, Michael Melcher, Michael Terrell, Moshe Ovadia, Natalie Guillen, Nikki Turner, Pam Fox Rollin, Priya Nalkur, Rebecca Zucker, Richard Hughes-Jones, Rick Winters, Rodrigo Lopez, Ronni Hendel-Giller, Scott Eblin, Stephanie Soler, Stephanie Stevens, Steve Magness, Steve Schlafman, Terra Winston, Tim Dorman, Tim Sullivan, Whitney Birdwell, Vineet Rajan

 

In memory of Roanak Desai and Erik Bengtsson, two people I was honored to know and to coach. RIP

 

Photo by Michael Whiffen.

Looking Under the Lamppost (On Problem-Solving)

A guy walking home one evening sees his neighbor staring at the street under a lamppost. "What are you looking for?" he asks.

"My house keys," the neighbor says. "I dropped them in the yard."

"Then why are you looking here?"

"The light's better."

That's a very old joke that comes up in my practice on a regular basis. [1] Why? Because it's how we often approach problem-solving. Rather than solve the problem that needs to be solved, we solve a problem that we want to solve.

Sometimes the problem that needs to be solved is outside our area of expertise. So we find another problem to solve, one that's under the lamppost, where the light's better.

Sometimes the problem that needs to be solved will take a long time to solve, and we want to feel "productive." So we find a whole bunch of little problems to solve that we can check off our to-do list.

Sometimes the problem that needs to be solved may truly be insoluble, and we're scared of trying and failing and looking foolish. So we find an easier problem to solve, one that will burnish our image and our ego.

These are all very understandable responses. Solving hard problems isn't merely an intellectual exercise, and sometimes we simply don't have what it takes to grope around in the dark, flailing endlessly, and occasionally having to admit defeat. But when we routinely limit ourselves to simple, small and solvable problems, we never develop the capacity to do anything else. Our comfort zones only grow when we get outside them.

This doesn't mean we should view ourselves harshly, without compassion. The fortitude to confront the problems that need to be solved can be derived from many sources, but it's more readily accessible when we invest in self-care practices that put us in the right state of mind and body. [2] Even then, we may lack confidence in our ability to solve these problems, but as I've noted before, "Confidence is a calculation of the odds of success. Courage is a calculation that the cost of not trying is higher than the cost of failing." [3]

And that latter calculation is far easier to make when we accept that our efforts to solve hard problems will often fail. This doesn't mean that we should be blasé or cavalier about failure. But when we view such failures as learning opportunities--"the ruling out of possibilities," in Peter Attia's phrase [4]--we realize that it's actually riskier to keep looking under the lamppost, where the light is, and the solutions to meaningful problems will only be found out there, in the dark.

 

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Footnote

[1] Apparently this joke was a staple of American newspapers starting in the 1920s.

[2] Investments, Not Indulgences

[3] Courage Isn't Confidence

[4] The Ruling Out of Possibilities

For Further Reading

The Traps We Set for Ourselves

The Obstacle Is the Way

Learning from Sisyphus

 

Photo by Abeeha Batool.